Flights to Chicago from CA $ 272*
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1 Passenger, Economy
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today
today
United's most popular flights to Chicago (ORD)
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CA $
Vancouver (YVR)to
Chicago (ORD)2026/02/25 - 2026/03/04
from
CA $ 631
Viewed: 2 hours ago
Roundtrip
Economy
Toronto (YYZ)to
Chicago (ORD)2026/02/12 - 2026/02/16
from
CA $ 303
Viewed: 2 hours ago
Roundtrip
Economy
Calgary (YYC)to
Chicago (ORD)2026/04/14 - 2026/04/28
from
CA $ 272
Viewed: 2 hours ago
Roundtrip
Economy
Montreal (YUL)to
Chicago (ORD)2026/02/19 - 2026/02/23
from
CA $ 283
Viewed: 3 hours ago
Roundtrip
Economy
Ottawa (YOW)to
Chicago (ORD)2026/05/27 - 2026/05/31
from
CA $ 781
Viewed: 1 day ago
Roundtrip
Economy
Québec (YQB)to
Chicago (ORD)2026/04/07 - 2026/04/11
from
CA $ 587
Viewed: 3 hours ago
Roundtrip
Economy
Edmonton (YEG)to
Chicago (ORD)2026/02/25 - 2026/03/04
from
CA $ 365
Viewed: 2 hours ago
Roundtrip
Economy
Winnipeg (YWG)to
Chicago (ORD)2026/03/02 - 2026/03/09
from
CA $ 728
Viewed: 19 hours ago
Roundtrip
Economy
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
Business class deals on flights to Chicago (ORD)
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flight_land
CA $
Vancouver (YVR)to
Chicago (ORD)
2026/03/07 - 2026/03/10
Roundtrip
Business
from
CA $ 1,391
Viewed: 17 hours ago
Toronto (YYZ)to
Chicago (ORD)
2026/02/12 - 2026/02/13
Roundtrip
Business
from
CA $ 790
Viewed: 7 hours ago
Calgary (YYC)to
Chicago (ORD)
2026/05/15 - 2026/05/24
Roundtrip
Business
from
CA $ 1,441
Viewed: 5 hours ago
Montreal (YUL)to
Chicago (ORD)
2026/02/18 - 2026/02/22
Roundtrip
Business
from
CA $ 516
Viewed: 7 hours ago
Ottawa (YOW)to
Chicago (ORD)
2026/05/27 - 2026/05/31
Roundtrip
Business
from
CA $ 1,117
Viewed: 1 day ago
Québec (YQB)to
Chicago (ORD)
2026/03/27 - 2026/03/29
Roundtrip
Business
from
CA $ 1,046
Viewed: 6 hours ago
Edmonton (YEG)to
Chicago (ORD)
2026/05/27 - 2026/05/31
Roundtrip
Business
from
CA $ 2,127
Viewed: 10 hours ago
Winnipeg (YWG)to
Chicago (ORD)
2026/05/15 - 2026/06/07
Roundtrip
Business
from
CA $ 1,065
Viewed: 1 day ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
Things to do after your flight to Chicago (ORD)
In Chicago, you can have it all
Chicago is the perfect urban getaway. “The Second City” is home to stunning architecture, endless shopping on the Magnificent Mile, one of the world’s most dynamic dining scenes, and a collection of critically acclaimed museums, all nestled on a lakefront lined with running trails and natural sand beaches.
Chicago’s top attractions
- Stroll through Millennium Park and take in the art and architecture, including Cloud Gate, which is also known as “The Bean,” Crown Fountain and Lurie Garden.
- Go shopping along the Magnificent Mile on Michigan Avenue.
- Discover the fun attractions at Navy Pier, including a large Ferris wheel, theater and carousel.
- Enjoy a day with the kids at the Shedd Aquarium and Lincoln Park Zoo.
- Tour Wrigley Field, home of the Chicago Cubs and one of the oldest baseball parks in the U.S.
- Take in city views from the Willis Tower’s Skydeck.
- Enjoy Chicago's family atractions.
Chicago is a popular place to visit all year round, though visitors will find that spring and fall have the most pleasant weather. Summertime activities include Lollapalooza music festival, Taste of Chicago, Chicago Jazz Festival and the Chicago Gay Pride Parade. Other major events throughout the year include the Chicago Underground Film Festival in the spring, the Chicago International Film Festival in the fall and the Magnificent Mile Lights Festival in the winter.
Find your vacation package to Chicago with United Packages.